1,4-Diethyl 2-formylbutanedioate → HCID 178470733, compound

HRID 481420

Reaction equation

HRID 481420 reaction equation
[Na].Cl.[CH3:3][O:4][CH2:5][C:6]([NH2:8])=[NH:7].[CH:9]([CH:11]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[C:12](OCC)=O)=[O:10]>C(O)C>[CH3:3][O:4][CH2:5][C:6]1[N:8]=[C:9]([OH:10])[C:11]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:12][N:7]=1

Participants

5

Reactant 3

HCID 2315001,4-Diethyl 2-formylbutanedioateHCID 5360545SodiumHCID 135486022-Methoxyethanimidamide hydrochloride

Product 1

HCID 178470733HCID 178470733, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Sodium metal (0.754 mol) was dissolved in absolute ethanol (100 ml) and the resulting solution was added dropwise to a solution of methoxyacetamidine hydrochloride (0.703 mol) in ethanol (100 ml). After 15 minutes the reaction mixture was filtered and the filtrate was added to a solution of diethyl formylsuccinate (0.703 mol), which was prepared according to H. Nakao et al. Ann. Sankyo Res. Lab., 18, 33-37 (1966). The reaction was refluxed for 15 hours, cooled to room temperature and was then concentrated to obtain a crude solid. This solid was crystallized from isopropanol to obtain the title compound (43% yield), m.p. 142°-143° C.

Workup

  1. filtrationAfter 15 minutes the reaction mixture was filtered
  2. customwas prepared
  3. temperatureThe reaction was refluxed for 15 hours
  4. concentrationwas then concentrated
  5. customto obtain a crude solid
  6. customThis solid was crystallized from isopropanol

Sources & evidence

ORD record
ord-587b3e7e02fd4e9f9937e0fcba93834b
Source dataset
uspto-grants-1998_08
Patent number
US05789415

Linked notes

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